Fmoc-Orn(Boc)-OH

Base Information

• Chemical Name: Fmoc-Orn(Boc)-OH
• CAS No.: 109425-55-0
• Molecular Formula: C25H30N2O6
• Molecular Weight: 454.523
• Hs Code.: 29242990
• European Community (EC) Number: 882-625-6
• DSSTox Substance ID: DTXSID00373246
• Nikkaji Number: J956.308C
• Mol file: 109425-55-0.mol

Synonyms:Fmoc-Orn(Boc)-OH;109425-55-0;Ndelta-Boc-Nalpha-Fmoc-L-ornithine;Nalpha-Fmoc-Ndelta-Boc-L-ornithine;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoic acid;(2S)-5-{[(tert-butoxy)carbonyl]amino}-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pentanoic acid;MFCD00065668;(2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-5-((2-methylpropan-2-yl)oxycarbonylamino)pentanoic acid;Fmoc-(Nd-Boc)-L-ornithine;N5-Boc-N2-Fmoc-L-ornithine;SCHEMBL1638340;DTXSID00373246;N-a-Boc-N-deta-Boc-L-ornithine;JOOIZTMAHNLNHE-NRFANRHFSA-N;AKOS015924224;AM10085;CS-W011572;AC-32121;AS-17433;B4184;Fmoc-Orn(Boc)-OH, >=96.0% (HPLC);EN300-262356;I10309;M03436;A802039;J-002278;S-109425-55-0;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-(tert-butoxycarbonylamino)pentanoic acid;(S)-5-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid;5-t-butoxycarbonylamino-(2S)-(9H-fluoren-9-ylmethoxycarbonyl amino)-pentanoic acid;5-t-butoxycarbonylamino-(2S)-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-delta-t-butyl-oxycarbonyl-L-ornithine;Ndelta-(tert-Butoxycarbonyl)-Nalpha-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-ornithine

Chemical Property of Fmoc-Orn(Boc)-OH

Chemical Property:

• Appearance/Colour: White powder with lumps
• Vapor Pressure: 2.28E-19mmHg at 25°C
• Melting Point: 111-115oC
• Refractive Index: 1.57
• Boiling Point: 679 °C at 760 mmHg
• PKA: 3.85±0.21(Predicted)
• Flash Point: 364.5 °C
• PSA: 113.96000
• Density: 1.226 g/cm³
• LogP: 5.06500
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 454.21038668
• Heavy Atom Count: 33
• Complexity: 669

Purity/Quality:

99% ^*data from raw suppliers

N-alpha-Fmoc-Nδ-Boc-L-ornithine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC(=O)NCCC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Technology Process of Fmoc-Orn(Boc)-OH

There total 10 articles about Fmoc-Orn(Boc)-OH which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + copper(II) complex of Nδ-tert-butoxycarbonyl-L-ornithine → Fmoc-Orn(Boc)-OH (109425-55-0,118476-89-4)

Guidance literature:

copper(II) complex of N^δ-tert-butoxycarbonyl-L-ornithine; With 8-quinolinol; sodium carbonate; In acetone; for 1h;

(fluorenylmethoxy)carbonyl chloride; With 1-hydroxy-pyrrolidine-2,5-dione; In water; at -5 ℃; for 0.5h;

DOI:10.1248/cpb.49.1189

Reference yield: 93.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + Nδ-(tert-butoxycarbonyl)-L-ornithine (13650-49-2,184576-63-4) → Fmoc-Orn(Boc)-OH (109425-55-0,118476-89-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

DOI:10.1002/psc.2968

Reference yield: 83.0%

Fmoc-Orn(Boc)-1,1-dimethylallyl ester (851713-95-6) → Fmoc-Orn(Boc)-OH (109425-55-0,118476-89-4)

Guidance literature:

With 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/ol0476117

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

di-tert-butyl dicarbonate

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

L-ornithine hydrochloride

Downstream raw materials:

Fmoc-Orn(Boc)-Phe(4NO₂)-NH₂

(S)-5-Amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid

cyclo-[SAA(Piv)-Val-Orn(Boc)-Leu-^DPhe-Pro-Val-Orn(Boc)-Leu]

Gramicidin S

Refernces

• 1、 Zhao, Yinan,Zhang, Shubiao,Zhang, Yuan,Cui, Shaohui,Chen, Huiying,Zhi, Defu,Zhen, Yuhong,Zhang, Shufen,Huang, Leaf. "Tri-peptide cationic lipids for gene delivery". . p. 119 - 126. Retrieved 2015.
• 2、 -. "COMPOUND FOR PREPARATION OF ANTIBODY-PAYLOAD CONJUGATE AND USE THEREOF". . . Retrieved 2022/03/15.
• 3、 -. "PROPYL CATIONIC PEPTIDE LIPIDS, SYNTHESIS METHOD THEREOF, AND APPLICATION THEREOF". Paragraph 0059; 0069; 0073; 0085. . Retrieved 2018/01/13.